تفاعل #40720

معادلة التفاعل

2-(benzo[d][1,3]dioxol-5-yl)acetic acid

thiocarbonohydrazide

thiopene-2-carbonyl chloride

NaHCO3

→

compound 2

3-((benzo[d][1,3]dioxol-5-yl)methyl)-6-(thiophen-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

المذيبات

MeOH CH2Cl2

chloride

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was cooled
2. 2
   غسيلThe organics were washed with water, saturated NaCl
3. 3
   تجفيفdried over Na2SO4
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىas is in the next reaction
6. 6
   درجة الحرارةwas refluxed 5 hours
7. 7
   أخرىThe excess phoshoryl chloride was removed under reduced pressure
8. 8
   workup.ADDITIONthe subsequent residue was mixed with crushed ice
9. 9
   ترشيحThe solids were filtered
10. 10
    غسيلwashed with water
11. 11
    أخرىdried in vaciio
12. 12
    أخرىPurification by reversed-phase HPLC

الإجراء التجريبي

As shown in FIG. 2, 2-(benzo[d][1,3]dioxol-5-yl)acetic acid (1 mmol) and thiocarbonohydrazide (1.5 mmol) were heated at 170° C. for 15 min. The mixture was cooled and taken up in 5% MeOH/CH2Cl2 and saturated NaHCO3. The organics were washed with water, saturated NaCl, dried over Na2SO4, and concentrated in vacuo. The resulting 5-((benzo[d][1,3]dioxol-5-yl)methyl)-4H-4-amino-3-mercapto-1,2,4-triazole (compound 1001) was used as is in the next reaction. Accordingly, a mixture of compound 1001 and thiopene-2-carbonyl chloride (0.176 g, 1.2 mmol) suspended in excess phoshoryl chloride (˜10 mL) was refluxed 5 hours. The excess phoshoryl chloride was removed under reduced pressure and the subsequent residue was mixed with crushed ice. The solids were filtered, washed with water, and dried in vaciio. Purification by reversed-phase HPLC produced pure 3-((benzo[d][1,3]dioxol-5-yl)methyl)-6-(thiophen-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (compound 2).

المصدر